Getting dressed is hard — so is committing to a mood as projected by your outfit. This is chiefly because if you’re the kind of dresser who truly appreciates, say, some feckless fringe, or a multi-tiered Flamenco-style skirt, who’s to say that just because you’ve elected to wear one of the two cited offerings, you’re willing to be typecast as she who is ready to rap battle ye old Western way or salsa dance like no digital emoji has ever danced before? Said accoutrements could frankly just be functioning as band-aids to assuage a good mood handicap.

And when you’re trying to evince several different vibes in one outfit, the game of dress-up gets even more confusing. Case in point: an e-mail I received from my friend last week requesting help with constructing the right outfit for a day that would include a. a job interview at a new fashion start-up in the afternoon and b. a super duper hot tamale rawr, let-me-roll-my-r’s date by nightfall. These two events would cushion the larger event of the rest of her day which is, you know, her current job in advertising.

I thought about what she should wear taking into account that the interview outfit had to elicit this sense of, “I have my shit together,” while the date outfit should have theoretically evoked the spirit of someone who can let her hair down freely, to flow like apple juice in a kindergarten class and stream like a river full of hyperbolic metaphor. She’s also not allowed to wear jeans to work which of course made my immediate and instinctive suggestion — high waist, flare leg jeans and a silk camisole + cardigan to take off later IF YOU KNOW WHAT I’M SAYING — null and void.

In continuing to mentally construct the outfit, I figured that she might be best suited to wear a pair of ivory trousers that fit slightly slouchy but still maintain the silhouette of her legs with a grey crew neck sweater over a white muscle tank (she will lose the sweater for her date), paired with loafers for the day (which say, “I’m confident enough to stand off heels and smart enough to know that you’d be an idiot not to hire me because I opted for flat shoes for this interview”) which she could conceivably keep on through the duration of her date (for the same reason, basically). But should she want to wear heels, that’s fine too; a pair of strappy somethings to highlight the pants’ slouch would work.

As for handbag? Something small. Because nothing says “my baggage is a carry-on” quite like, you know, a minute carry-on.

Also: consider a selection of dainty-ass-but-cute gold necklaces and a wrist of thick bangles for…uh…posterity.

Do you find yourself in a similar dilemma? Was this helpful? Do you want more outfit advice? TELL ME FOR WHAT. I WILL SERVE IT TO YOU ON A NONREFUNDABLE SILVER PLATTER.

I KNOW WHAT YOU’RE SAYING LEA!
(Is it ok if us readers start adopting you personal monicker?

Jenny

Beyond helpful! What about an outfit for NYU Hillel’s Matzah-Ball? It’s a saturday night party and there will be a ton of NJB’s..http://www.americantrender.com

Kimberly

This is great! The outfit is great. The writing is great. You’re great! What would you wear to hang out at a coffee shop looking like I don’t care but I still like outstanding. Casual, impressive outfits please!

Leandra Medine

I feel like….just put a nicely fitting trench coat over whatever you’re wearing. I’m exceptionally obsessed in a non-hyperbolic way with this one: http://bit.ly/1dAWPbS

Help me! I work in a creative shop, but I am the only girl in my office. I am pretty man repeller outside the office, but it feels really dramatic for my day to day. I am sick of dressing like the boys. Don’t get me wrong, I love menswear, I got that down. But I want to wear more feminine stuff without looking too prissy. Any ideas?

Leandra Medine

How about girly-ass a-line dressed with more chunky shoes. Like some buckly wedges or a pair of gladiators? Another easy default: put a leather jacket over anything and watch it immediately transform.

http://www.cakeoverholt.com definitely not kate

Wow! My very own Man Repeller outfit (TM)!!!! I will try it out. Thank you.

Juliet

I’m sorry but that outfit is horrible, love the accessories, but an a-line sleeveless dress would be more appropriate and enticing than this white t-shirt + ivory pants combo

Johanna

I like it! A MR classic, if there is such a thing….

Mihkayla M.

Dear Team Manrepeller,
So yesterday I saw this cute guy that works at Barnes & Nobles, but I don’t know
how to approach him (or if I even should). I HATE the thought of being rejected so much that I’m already talking myself out of even initiating anything. What do you think I should do? I thought you’d be the best people to ask, since we’re cyber bffs. Also he happens to be Caucasian and I happen to be African American, so I already feel out of my comfort zone. I’ve never dated outside my race before. Not intentionally, it just kind of happened like that.

Thanks,
Your friend Mihkayla

Leandra Medine

M-cat. Talk to him. The worst comes to it he says thanks but no thanks in which you marvel in the thought that you’re nt working hard enough/doing a good enough job if you DONT get told no every now and again.

OK. SINCE YOU’RE OFFERING: I’m going to San Fran for work/play next week (Amelia, I think you’ve mentioned you’re from there, right?) and the play aspect will be three days prior to my work aspect. The work aspect is bizznazz attire from 7am-6pm, then I can put on play-ish attire, but still have to keep in mind I’ll be with all work people that I am younger than by 20+ years. I did this exact trip in the fall, and I felt very boring. There may even be a reception at night that is semi-formal but not super over the top formal. SO I AM DRESSING FOR SO MANY THINGS. I don’t want to bring one million bags soooooo ideas?!

Sincerely,
Feeling Suitcased in Boston.

Leandra Medine

Do you have a very reliable skirt that moonlights as your co worker AND your drinking buddy? Pick one solid chameleonic piece and work around that shit accordingly.

http://adeliberateimagination.wordpress.com/ CJKEYS2

No, but that is a great call, and I will now try to find one before Thursday. Thank you!

This was very helpful, and also made me realize how I put no thought or effort at all into any of my dressing choices even when I should like for special events like these: date and job interview. *grabs a brownie bite in remorse and rethinks her entire life*

Rad

I’ve been waiting for something like this!
I have my Year 12 formal (or prom? as you call it in America) coming up and I am just confused on what to wear..
Help me?

Leandra Medine

One word: TUXEDO

Namrata

High waisted palazzo pants and a crop-top with a blazer over. Chuck the blazer, and add some bling for the night!

Challenge: I work in a kilt shop. How to make mini women’s kilts manrepellent?

Leandra Medine

gurlfriend! don’t shave your legs.

LB

I’m the singer in an awesome garage rock band. I make all the guys in my band wear suits and ties. Any ideas for a tragic-barfly-goth-goes-uptown look? My style cues are Saint Laurent and Iggy Pop. Thanks!

http://www.fancyalterego.wordpress.com/ Heather P.

I’m married, so I’m not really sure what a “date” looks like.

I do like the different take on job interview clothing, though. As someone who is about to throw herself into the ring of job interviews again, I’m always looking for ways to stand out among the sea of black pantsuits!